Preheat your oven to 204 °C (200 °C) and line a large rimmed baking sheet with parchment paper.

Add the diced bacon to a skillet over medium heat and cook for 5 to 6 minutes until partially crisp and rendered, then transfer to a paper towel-lined plate.

Place the halved Brussels sprouts in a large mixing bowl, toss with olive oil, kosher salt, and black pepper until evenly coated, then fold in half of the rendered bacon.

Arrange the Brussels sprouts cut-side down in an even, single layer on the prepared baking sheet, leaving space between them.

Roast for 20 to 22 minutes until the bottoms are deeply browned and caramelized and the sprouts are tender when pierced with a fork.

While roasting, whisk together the balsamic vinegar, honey, and red pepper flakes in a small bowl until completely combined and emulsified.

Transfer the roasted Brussels sprouts to a serving platter, scatter the remaining crispy bacon over top, and drizzle with the honey balsamic glaze right before serving.